Running from commitments and failures, two college buddies romp through California, sampling the
local wine—and women—in Sideways.

Sideways is the sweetest, funniest, most humane movie I’ve seen all year. I emphasize its humanity because most of what passes for comedy these days, whether it be low-concept or smarty-pants, is little more than gagfests peopled by joke-bots. In the movies and on television, it’s become hip to make comedies about nothing, à la Seinfeld and Curb Your Enthusiasm, or, in the case of I Love Huckabees, everything—which might as well be nothing. Frosty facetiousness is the signature style of the new “intellectual” American jape, and until now, I would have lumped Alexander Payne—who directed Sideways and adapted it from a Rex Pickett novel with his partner, Jim Taylor—into a mix that includes such prodigious smart alecks as Paul Thomas Anderson, the Coen brothers, and David O. Russell. In his previous feature films, Citizen Ruth, Election, and particularly About Schmidt, all of which were set in his native Nebraska, Payne was keen on displaying his own superiority to his characters. His movies were
vehicles for vengeance against the heartland. (No yokel he.) But somewhere between his last film and his new one, Payne traded in his sarcasm for a soul. Maybe it has something to do with the fact that Sideways is set in the golden pastoral haze of California’s Central Coast wine country. Or maybe it was just all that wine.

Paul Giamatti’s Miles, a woebegone eighth-grade English teacher and would-be novelist, is the film’s unlikely Pinot aficionado who sets off from L.A. on a wine-tasting trip with Jack (Thomas Haden Church), an old college friend and washed-up actor, the week before Jack’s wedding. Miles is still sulking two years after his divorce from a woman he still pines for; Jack, who has large, rangy features and big hair and a surfer dude’s deep drawl, aims to cheer him up by getting him laid—a cure-all that he also reserves for himself. (He calls this trip his “last week of freedom.”) All the standard clichés are in place for a midlife-crisis, buddies-on-the-road movie, except that none of it plays out the way you’d expect. These guys may be an odd couple, but the mismatch makes psychological sense: Miles confers a connoisseurship on his friend, who doesn’t read much and thinks all wines taste pretty much the same; Jack stokes Miles’s id. If they had met as adults, they would probably not have connected, but college friendships are forged at a time when everyone is experimenting with who they are.

In each other’s company, the experiment resumes. Miles and Jack knock about as if they were still late-stage adolescents. They’re still figuring out who they want to be, which gives their strenuous efforts at happiness an added poignancy (and absurdity). We can see that Miles, who according to Jack has been “officially depressed for, like, two years,” is more than just a glum zhlub; he may not be able to get his book sold, but his love of language is as real as his love of the grape. When he talks about literature or his favorite wines, he isn’t showing off. He’s trying to live up to his own best image of himself, and he seems transported. In his own dim way, Jack understands this, which is why their friendship is more complicated than it appears. Jack is always telling the people they meet that Miles’s book is being published, and he isn’t being cruel—he’s trying to inspire Miles to be the guy he was before the two-year tailspin (and also get him some action).

“Paul Giamatti
isn’t simply replaying Harvey Pekar
from American Splendor—this is
a whole other species of depresso.”

Miles has a wonderful monologue in which he rhapsodizes about the Pinot grape to a sympathetic waitress, Maya (an extraordinarily good Virginia Madsen). He calls it thin-skinned, temperamental, in need of constant care and
attention. Of course, he is talking about himself. (Jack, by contrast, is a Cabernet that can grow anywhere and thrive even when neglected.) Miles is preternaturally sensitive to his own shortcomings. When Maya, who also knows her wine, leaves him an opening to make a pass, he lets the moment slide away, and his misery shines forth from his eyes like a death ray. Giamatti is letting us know that Miles’s eloquence about wine may just be a fancy way of tarting up his drinking habit, his sadness. But he isn’t simply replaying his Harvey Pekar from American Splendor—this is a whole other species of depresso: tender, enraged, rueful about what he has lost. At least Pekar was published.

One of the wonderful things about Sideways is that Payne gives its women equal standing (that’s why it’s not really a buddy movie). Maya is every bit as intricate as Miles—she has her own self-revealing monologue about how wine is “actually alive,” gaining complexity until its inevitable decline. But she’s blunter than he is. She tells him she loves wine because, when all is said and done, it “tastes so fucking good.” Hard knocks haven’t bruised her the way they have Miles; she’s still in the game, going for a degree in horticulture and taking things as they come. Miles may be one of those things, but she doesn’t press it—she respects his grief, and she’s also a little wary of it.

Maya’s friend Stephanie (Sandra Oh), a local wine pourer, is the film’s freest spirit, and an ideal playmate for Jack. Their carnal romps, at least until Stephanie finds out Jack is engaged, are great lewd slapstick. Miles chastises his friend, but it’s hard to argue with the guy’s life force, which is so outsize it’s comic. Jack has an actor’s penchant for playing everything center stage; when he’s recognized by a waitress for some crummy, long-ago soap-opera role, he acquires an imbecilic glow—he’s in clover. (Soon after, he’s in her bed.) Thomas Haden Church is known primarily for the inane sitcom Wings, so his performance here is a revelation: He gives depth to shallowness. Jack the satyr-narcissist is a figure of fun, but he harbors his own losses. That’s why he plumps up every time he’s noticed. He compensates for his show-business failure by converting the world into his very own playhouse.

Miles and Jack, in their own ways, are in awe of women—of their power to scramble a man’s good sense. Miles’s ex-wife, when we finally meet her, is no gorgon; she’s decent and intelligent and still cares about him, only not enough. With Miles, declarations of faith are supposed to be forever. He can’t abide the waywardness of affection, any more than he can abide someone who doesn’t love Pinot. In Sideways, wine is much more than wine. It’s a metaphor for the spirits that bring us to a reckoning with ourselves.